CTO Confessions Brought to you by IT Labs · 2026-05-12 · 52 min
Background checks sound straightforward. Until you try to build the infrastructure behind them at scale. In this episode of CTO Confessions, TC Gill sits down with Luca Bonmassar, CTO of Checkr - a platform that helps millions of people find meaningful work and helps companies hire with confidence. Luca brings over 20 years of experience across Fintech, Crypto, Social Media, and AI/ML, and has co-founded and sold three startups. He's one of the rare CTOs who moves as comfortably in a business conversation as a technical one. In this episode: → Why understanding the business side isn't optional for a CTO → The surprising complexity of data that still exists only in physical form → Why hiring fast and firing faster may cost you more than you think → His philosophy on over-engineering - and why patience often wins "It's better to be late knowing that what you build will have greater impact than building things and hoping someone will use them one day."
Episode 206: Dissecting the CTO Role Misconceptions, Hiring, and the Age of AI with Jay Dalke59 / 100Episode 204: How fast is technology evolving with Ahmed AbdelrahmanEpisode 203: Getting Priorities & Requirements Right with Rigvinath Chevala
Episode 202: Your system doesn’t need heroes - A guide on building and scaling a teamEpisode 201: What it takes to build great innovative hardware with Nico Cormier